When plugging in my headset, the sound continues to play on the ipad and not on the heeadset. Why?

When plugging in my headset in my iPad, the sound continues to play on the ipad and does not switch to the heeadset. Why? I did not have this problem before.

If you have used earphones in the past then I assume that you realize it takes a very firm push to insert the headphones into the opening - correct?

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